RU2008145871A - Антагонисты рецептора il-8 - Google Patents
Антагонисты рецептора il-8 Download PDFInfo
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- RU2008145871A RU2008145871A RU2008145871/04A RU2008145871A RU2008145871A RU 2008145871 A RU2008145871 A RU 2008145871A RU 2008145871/04 A RU2008145871/04 A RU 2008145871/04A RU 2008145871 A RU2008145871 A RU 2008145871A RU 2008145871 A RU2008145871 A RU 2008145871A
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- Prior art keywords
- chloro
- urea
- hydroxyphenyl
- phenyl
- oct
- Prior art date
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- 108090001007 Interleukin-8 Proteins 0.000 title claims 3
- 239000002464 receptor antagonist Substances 0.000 title 1
- 229940044551 receptor antagonist Drugs 0.000 title 1
- -1 phenyloxy Chemical group 0.000 claims abstract 50
- 150000001875 compounds Chemical class 0.000 claims abstract 26
- 125000000217 alkyl group Chemical group 0.000 claims abstract 20
- 229910052736 halogen Inorganic materials 0.000 claims abstract 12
- 150000002367 halogens Chemical group 0.000 claims abstract 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 12
- 125000001424 substituent group Chemical group 0.000 claims abstract 9
- 125000004122 cyclic group Chemical group 0.000 claims abstract 6
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 6
- 239000001257 hydrogen Substances 0.000 claims abstract 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract 6
- 150000003839 salts Chemical class 0.000 claims abstract 6
- 125000006555 (C3-C5) cycloalkyl group Chemical group 0.000 claims abstract 4
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims abstract 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims abstract 2
- 229910052801 chlorine Inorganic materials 0.000 claims abstract 2
- 239000000460 chlorine Substances 0.000 claims abstract 2
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 29
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 9
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 8
- 201000010099 disease Diseases 0.000 claims 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 8
- 108010012236 Chemokines Proteins 0.000 claims 7
- 102000019034 Chemokines Human genes 0.000 claims 7
- 241000124008 Mammalia Species 0.000 claims 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 6
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 5
- 125000003545 alkoxy group Chemical group 0.000 claims 5
- 125000006309 butyl amino group Chemical group 0.000 claims 5
- 230000001404 mediated effect Effects 0.000 claims 5
- 238000000034 method Methods 0.000 claims 5
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims 4
- 208000013616 Respiratory Distress Syndrome Diseases 0.000 claims 4
- 208000011341 adult acute respiratory distress syndrome Diseases 0.000 claims 4
- 201000000028 adult respiratory distress syndrome Diseases 0.000 claims 4
- 208000006673 asthma Diseases 0.000 claims 4
- RNNBGAHBGNJAGE-UHFFFAOYSA-N 1-[4-chloro-3-(3,8-diazabicyclo[3.2.1]octan-3-ylsulfonyl)-2-hydroxyphenyl]-3-(2-phenoxyphenyl)urea Chemical compound C1=CC(Cl)=C(S(=O)(=O)N2CC3CCC(N3)C2)C(O)=C1NC(=O)NC1=CC=CC=C1OC1=CC=CC=C1 RNNBGAHBGNJAGE-UHFFFAOYSA-N 0.000 claims 3
- HONMASBTBAPAJJ-UHFFFAOYSA-N 1-[4-chloro-3-(3,8-diazabicyclo[3.2.1]octan-3-ylsulfonyl)-2-hydroxyphenyl]-3-(3-fluoro-2-methylphenyl)urea Chemical compound CC1=C(F)C=CC=C1NC(=O)NC1=CC=C(Cl)C(S(=O)(=O)N2CC3CCC(N3)C2)=C1O HONMASBTBAPAJJ-UHFFFAOYSA-N 0.000 claims 3
- AUIYZBPIYFZKJY-GOOCMWNKSA-N 1-[4-chloro-3-[[(1r,5s)-3-(cyclopropylamino)-8-azabicyclo[3.2.1]octan-8-yl]sulfonyl]-2-hydroxyphenyl]-3-(2-chloro-3-fluorophenyl)urea Chemical compound C([C@]1(CC[C@@](C2)(N1S(=O)(=O)C=1C(=C(NC(=O)NC=3C(=C(F)C=CC=3)Cl)C=CC=1Cl)O)[H])[H])C2NC1CC1 AUIYZBPIYFZKJY-GOOCMWNKSA-N 0.000 claims 3
- UKEODWQYKLFNKV-AGUYFDCRSA-N 1-[4-chloro-3-[[(1r,5s)-3-(ethylamino)-8-azabicyclo[3.2.1]octan-8-yl]sulfonyl]-2-hydroxyphenyl]-3-(2-chloro-3-fluorophenyl)urea Chemical compound N1([C@]2([H])CC[C@]1(CC(C2)NCC)[H])S(=O)(=O)C(C(=CC=1)Cl)=C(O)C=1NC(=O)NC1=CC=CC(F)=C1Cl UKEODWQYKLFNKV-AGUYFDCRSA-N 0.000 claims 3
- WUMHAFGYRJQVAA-MQVJKMGUSA-N 1-[4-chloro-3-[[(1r,5s)-3-(ethylamino)-8-azabicyclo[3.2.1]octan-8-yl]sulfonyl]-2-hydroxyphenyl]-3-(3-fluoro-2-methylphenyl)urea Chemical compound N1([C@]2([H])CC[C@]1(CC(C2)NCC)[H])S(=O)(=O)C(C(=CC=1)Cl)=C(O)C=1NC(=O)NC1=CC=CC(F)=C1C WUMHAFGYRJQVAA-MQVJKMGUSA-N 0.000 claims 3
- DNOKBVYRPWLULP-UWVGGRQHSA-N 1-[4-chloro-3-[[(1s,4s)-2,5-diazabicyclo[2.2.1]heptan-2-yl]sulfonyl]-2-hydroxyphenyl]-3-(2-chloro-3-fluorophenyl)urea Chemical compound C([C@]1(NC[C@]2([H])C1)[H])N2S(=O)(=O)C(C=1O)=C(Cl)C=CC=1NC(=O)NC1=CC=CC(F)=C1Cl DNOKBVYRPWLULP-UWVGGRQHSA-N 0.000 claims 3
- XGGAKJCYUCGHMZ-PHIMTYICSA-N 1-[4-chloro-3-[[(1s,5r)-3,8-diazabicyclo[3.2.1]octan-8-yl]sulfonyl]-2-hydroxyphenyl]-3-(2-chloro-3-fluorophenyl)urea Chemical compound N1([C@]2([H])CC[C@]1(CNC2)[H])S(=O)(=O)C(C(=CC=1)Cl)=C(O)C=1NC(=O)NC1=CC=CC(F)=C1Cl XGGAKJCYUCGHMZ-PHIMTYICSA-N 0.000 claims 3
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims 3
- 206010040070 Septic Shock Diseases 0.000 claims 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 3
- 239000004202 carbamide Substances 0.000 claims 3
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 3
- ZGFRYCRDXCTXBA-QWRGUYRKSA-N 1-(2-chloro-3-fluorophenyl)-3-[4-chloro-2-hydroxy-3-[[(1s,4s)-5-methyl-2,5-diazabicyclo[2.2.1]heptan-2-yl]sulfonyl]phenyl]urea Chemical compound C([C@]1(N(C[C@]2([H])C1)C)[H])N2S(=O)(=O)C(C(=CC=1)Cl)=C(O)C=1NC(=O)NC1=CC=CC(F)=C1Cl ZGFRYCRDXCTXBA-QWRGUYRKSA-N 0.000 claims 2
- HSBKLRQSRFANNZ-UHFFFAOYSA-N 1-[4-chloro-3-(1,8-diazaspiro[4.5]decan-8-ylsulfonyl)-2-hydroxyphenyl]-3-(2-chloro-3-fluorophenyl)urea Chemical compound C1=CC(Cl)=C(S(=O)(=O)N2CCC3(NCCC3)CC2)C(O)=C1NC(=O)NC1=CC=CC(F)=C1Cl HSBKLRQSRFANNZ-UHFFFAOYSA-N 0.000 claims 2
- DWMIADSRLTYJBG-UHFFFAOYSA-N 1-[4-chloro-3-(1,8-diazaspiro[4.5]decan-8-ylsulfonyl)-2-hydroxyphenyl]-3-(3-fluoro-2-methylphenyl)urea Chemical compound CC1=C(F)C=CC=C1NC(=O)NC1=CC=C(Cl)C(S(=O)(=O)N2CCC3(NCCC3)CC2)=C1O DWMIADSRLTYJBG-UHFFFAOYSA-N 0.000 claims 2
- ACQFHYAQGLSNAC-UHFFFAOYSA-N 1-[4-chloro-3-(6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-ylsulfonyl)-2-hydroxyphenyl]-3-(2-chloro-3-fluorophenyl)urea Chemical compound C1=CC(Cl)=C(S(=O)(=O)N2CC3=NC=CN3CC2)C(O)=C1NC(=O)NC1=CC=CC(F)=C1Cl ACQFHYAQGLSNAC-UHFFFAOYSA-N 0.000 claims 2
- DNOKBVYRPWLULP-ZJUUUORDSA-N 1-[4-chloro-3-[[(1s,4r)-2,5-diazabicyclo[2.2.1]heptan-2-yl]sulfonyl]-2-hydroxyphenyl]-3-(2-chloro-3-fluorophenyl)urea Chemical compound C([C@@]1(NC[C@]2([H])C1)[H])N2S(=O)(=O)C(C=1O)=C(Cl)C=CC=1NC(=O)NC1=CC=CC(F)=C1Cl DNOKBVYRPWLULP-ZJUUUORDSA-N 0.000 claims 2
- UNIWORFJYDXWQB-HOTGVXAUSA-N 1-[4-chloro-3-[[(1s,4s)-2,5-diazabicyclo[2.2.1]heptan-2-yl]sulfonyl]-2-hydroxyphenyl]-3-(2-phenoxyphenyl)urea Chemical compound C([C@]1(NC[C@]2([H])C1)[H])N2S(=O)(=O)C(C=1O)=C(Cl)C=CC=1NC(=O)NC1=CC=CC=C1OC1=CC=CC=C1 UNIWORFJYDXWQB-HOTGVXAUSA-N 0.000 claims 2
- QKZATTLECOGXEB-ROUUACIJSA-N 1-[4-chloro-3-[[(1s,4s)-2,5-diazabicyclo[2.2.1]heptan-2-yl]sulfonyl]-2-hydroxyphenyl]-3-(2-phenylmethoxyphenyl)urea Chemical compound C([C@]1(NC[C@]2([H])C1)[H])N2S(=O)(=O)C(C=1O)=C(Cl)C=CC=1NC(=O)NC1=CC=CC=C1OCC1=CC=CC=C1 QKZATTLECOGXEB-ROUUACIJSA-N 0.000 claims 2
- NBNZDLOYGFNKSX-PHIMTYICSA-N 1-[4-chloro-3-[[(1s,5r)-3,8-diazabicyclo[3.2.1]octan-3-yl]sulfonyl]-2-hydroxyphenyl]-3-(2-chloro-3-fluorophenyl)urea Chemical compound C([C@]1(CC[C@@](C2)(N1)[H])[H])N2S(=O)(=O)C(C(=CC=1)Cl)=C(O)C=1NC(=O)NC1=CC=CC(F)=C1Cl NBNZDLOYGFNKSX-PHIMTYICSA-N 0.000 claims 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 2
- WQKHERPPDYPMNX-UHFFFAOYSA-N 6-chloro-3,4-dihydro-2h-naphthalen-1-one Chemical compound O=C1CCCC2=CC(Cl)=CC=C21 WQKHERPPDYPMNX-UHFFFAOYSA-N 0.000 claims 2
- 102000012740 beta Adrenergic Receptors Human genes 0.000 claims 2
- 108010079452 beta Adrenergic Receptors Proteins 0.000 claims 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- CHWTWYIXLKQNQB-UHFFFAOYSA-N 1-[3-(1,2,3,3a,4,6,7,7a-octahydropyrrolo[3,2-c]pyridin-5-ylsulfonyl)-4-chloro-2-hydroxyphenyl]-3-(2-chloro-3-fluorophenyl)urea Chemical compound C1=CC(Cl)=C(S(=O)(=O)N2CC3CCNC3CC2)C(O)=C1NC(=O)NC1=CC=CC(F)=C1Cl CHWTWYIXLKQNQB-UHFFFAOYSA-N 0.000 claims 1
- SEGNSEUXIMDNPI-UHFFFAOYSA-N 1-[3-(1,2,3,3a,4,6,7,7a-octahydropyrrolo[3,2-c]pyridin-5-ylsulfonyl)-4-chloro-2-hydroxyphenyl]-3-(2-chloropyridin-3-yl)urea Chemical compound C1=CC(Cl)=C(S(=O)(=O)N2CC3CCNC3CC2)C(O)=C1NC(=O)NC1=CC=CN=C1Cl SEGNSEUXIMDNPI-UHFFFAOYSA-N 0.000 claims 1
- MSWCEQJQBLVFIL-UHFFFAOYSA-N 1-[3-(1,2,3,3a,4,6,7,7a-octahydropyrrolo[3,2-c]pyridin-5-ylsulfonyl)-4-chloro-2-hydroxyphenyl]-3-(3-fluoro-2-methylphenyl)urea Chemical compound CC1=C(F)C=CC=C1NC(=O)NC1=CC=C(Cl)C(S(=O)(=O)N2CC3CCNC3CC2)=C1O MSWCEQJQBLVFIL-UHFFFAOYSA-N 0.000 claims 1
- QLMRDUBUVLKBGI-UHFFFAOYSA-N 1-[3-[(3-benzyl-3,8-diazabicyclo[3.2.1]octan-8-yl)sulfonyl]-4-chloro-2-hydroxyphenyl]-3-(2-chloro-3-fluorophenyl)urea Chemical compound C1=CC(Cl)=C(S(=O)(=O)N2C3CCC2CN(CC=2C=CC=CC=2)C3)C(O)=C1NC(=O)NC1=CC=CC(F)=C1Cl QLMRDUBUVLKBGI-UHFFFAOYSA-N 0.000 claims 1
- ZDJFKZQIMPXIHG-UHFFFAOYSA-N 1-[4-chloro-3-(1,8-diazaspiro[4.5]decan-8-ylsulfonyl)-2-hydroxyphenyl]-3-(2-ethylphenyl)urea Chemical compound CCC1=CC=CC=C1NC(=O)NC1=CC=C(Cl)C(S(=O)(=O)N2CCC3(NCCC3)CC2)=C1O ZDJFKZQIMPXIHG-UHFFFAOYSA-N 0.000 claims 1
- RCYAOPOAKRDRPB-UHFFFAOYSA-N 1-[4-chloro-3-(1,8-diazaspiro[4.5]decan-8-ylsulfonyl)-2-hydroxyphenyl]-3-[2-(trifluoromethoxy)phenyl]urea Chemical compound C1=CC(Cl)=C(S(=O)(=O)N2CCC3(NCCC3)CC2)C(O)=C1NC(=O)NC1=CC=CC=C1OC(F)(F)F RCYAOPOAKRDRPB-UHFFFAOYSA-N 0.000 claims 1
- OZVJRQMLLBIHEU-UHFFFAOYSA-N 1-[4-chloro-3-(3,8-diazabicyclo[3.2.1]octan-3-ylsulfonyl)-2-hydroxyphenyl]-3-(2-chloropyridin-3-yl)urea Chemical compound C1=CC(Cl)=C(S(=O)(=O)N2CC3CCC(N3)C2)C(O)=C1NC(=O)NC1=CC=CN=C1Cl OZVJRQMLLBIHEU-UHFFFAOYSA-N 0.000 claims 1
- BYWCEVIRMLRAOU-UHFFFAOYSA-N 1-[4-chloro-3-(6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-ylsulfonyl)-2-hydroxyphenyl]-3-(2-chloropyridin-3-yl)urea Chemical compound C1=CC(Cl)=C(S(=O)(=O)N2CC3=NC=CN3CC2)C(O)=C1NC(=O)NC1=CC=CN=C1Cl BYWCEVIRMLRAOU-UHFFFAOYSA-N 0.000 claims 1
- ARHDPHGWDPKXBY-UHFFFAOYSA-N 1-[4-chloro-3-(6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-ylsulfonyl)-2-hydroxyphenyl]-3-(2-ethylphenyl)urea Chemical compound CCC1=CC=CC=C1NC(=O)NC1=CC=C(Cl)C(S(=O)(=O)N2CC3=NC=CN3CC2)=C1O ARHDPHGWDPKXBY-UHFFFAOYSA-N 0.000 claims 1
- CAEYRRAGTFPSHP-NXEZZACHSA-N 1-[4-chloro-3-[[(1r,4r)-2,5-diazabicyclo[2.2.1]heptan-2-yl]sulfonyl]-2-hydroxyphenyl]-3-(2-chloropyridin-3-yl)urea Chemical compound C([C@@]1(NC[C@@]2([H])C1)[H])N2S(=O)(=O)C(C=1O)=C(Cl)C=CC=1NC(=O)NC1=CC=CN=C1Cl CAEYRRAGTFPSHP-NXEZZACHSA-N 0.000 claims 1
- MDNQCHUMXKZCIP-ZIAGYGMSSA-N 1-[4-chloro-3-[[(1r,4r)-2,5-diazabicyclo[2.2.1]heptan-2-yl]sulfonyl]-2-hydroxyphenyl]-3-(2-ethylphenyl)urea Chemical compound C([C@@]1(NC[C@@]2([H])C1)[H])N2S(=O)(=O)C(C=1O)=C(Cl)C=CC=1NC(=O)NC1=CC=CC=C1CC MDNQCHUMXKZCIP-ZIAGYGMSSA-N 0.000 claims 1
- PYNFRFIWPMMKGG-TXEJJXNPSA-N 1-[4-chloro-3-[[(1r,5s)-3,7-diazabicyclo[3.3.1]nonan-3-yl]sulfonyl]-2-hydroxyphenyl]-3-(2-chloropyridin-3-yl)urea Chemical compound C([C@]1(CNC[C@@](C2)(C1)[H])[H])N2S(=O)(=O)C(C=1O)=C(Cl)C=CC=1NC(=O)NC1=CC=CN=C1Cl PYNFRFIWPMMKGG-TXEJJXNPSA-N 0.000 claims 1
- HDNYZFWDYAMMPN-RYUDHWBXSA-N 1-[4-chloro-3-[[(1s,4s)-2,5-diazabicyclo[2.2.1]heptan-2-yl]sulfonyl]-2-hydroxyphenyl]-3-(3-fluoro-2-methylphenyl)urea Chemical compound C([C@]1(NC[C@]2([H])C1)[H])N2S(=O)(=O)C(C(=CC=1)Cl)=C(O)C=1NC(=O)NC1=CC=CC(F)=C1C HDNYZFWDYAMMPN-RYUDHWBXSA-N 0.000 claims 1
- QTUGLJDVKLICCA-GASCZTMLSA-N 1-[4-chloro-3-[[(1s,5r)-3,8-diazabicyclo[3.2.1]octan-3-yl]sulfonyl]-2-hydroxyphenyl]-3-(2-ethylphenyl)urea Chemical compound C([C@]1(CC[C@@](C2)(N1)[H])[H])N2S(=O)(=O)C(C(=CC=1)Cl)=C(O)C=1NC(=O)NC1=CC=CC=C1CC QTUGLJDVKLICCA-GASCZTMLSA-N 0.000 claims 1
- JQIFEPXTEHAMOS-GASCZTMLSA-N 1-[4-chloro-3-[[(1s,5r)-3,8-diazabicyclo[3.2.1]octan-8-yl]sulfonyl]-2-hydroxyphenyl]-3-(2-ethylphenyl)urea Chemical compound N1([C@]2([H])CC[C@]1(CNC2)[H])S(=O)(=O)C(C(=CC=1)Cl)=C(O)C=1NC(=O)NC1=CC=CC=C1CC JQIFEPXTEHAMOS-GASCZTMLSA-N 0.000 claims 1
- APKOVQXQUOWYQH-RYUDHWBXSA-N 1-[4-chloro-3-[[(1s,5s)-3,7-diazabicyclo[3.3.1]nonan-3-yl]sulfonyl]-2-hydroxyphenyl]-3-(2-chloro-3-fluorophenyl)urea Chemical compound C([C@@]1(CNC[C@@](C2)(C1)[H])[H])N2S(=O)(=O)C(C=1O)=C(Cl)C=CC=1NC(=O)NC1=CC=CC(F)=C1Cl APKOVQXQUOWYQH-RYUDHWBXSA-N 0.000 claims 1
- 125000005983 2,5-diazabicyclo[2.2.1]heptan-2-yl group Chemical group 0.000 claims 1
- 125000004938 5-pyridyl group Chemical group N1=CC=CC(=C1)* 0.000 claims 1
- ZERCTXGMBRAWQP-UHFFFAOYSA-N 8-azabicyclo[3.2.1]octan-3-amine Chemical group C1C(N)CC2CCC1N2 ZERCTXGMBRAWQP-UHFFFAOYSA-N 0.000 claims 1
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- 206010044248 Toxic shock syndrome Diseases 0.000 claims 1
- 231100000650 Toxic shock syndrome Toxicity 0.000 claims 1
- 201000006704 Ulcerative Colitis Diseases 0.000 claims 1
- 239000013543 active substance Substances 0.000 claims 1
- 125000003282 alkyl amino group Chemical group 0.000 claims 1
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- 239000003085 diluting agent Substances 0.000 claims 1
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- 125000005843 halogen group Chemical group 0.000 claims 1
- 210000003958 hematopoietic stem cell Anatomy 0.000 claims 1
- 239000013067 intermediate product Substances 0.000 claims 1
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- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
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- 125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract 4
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
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| US8648118B2 (en) * | 2010-12-17 | 2014-02-11 | Boehringer Ingelheim International Gmbh | Bicyclic ring system substituted amide functionalised phenols as medicaments |
| US9241930B2 (en) | 2011-08-24 | 2016-01-26 | Novadrug, Llc | Compositions and methods for treating viral diseases |
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-
2007
- 2007-04-20 MX MX2008013599A patent/MX2008013599A/es not_active Application Discontinuation
- 2007-04-20 US US12/297,917 patent/US8097626B2/en not_active Expired - Fee Related
- 2007-04-20 AU AU2007240364A patent/AU2007240364A1/en not_active Abandoned
- 2007-04-20 CN CNA2007800232115A patent/CN101495113A/zh active Pending
- 2007-04-20 CA CA002650007A patent/CA2650007A1/en not_active Abandoned
- 2007-04-20 WO PCT/US2007/067088 patent/WO2007124423A2/en not_active Ceased
- 2007-04-20 EP EP07761016A patent/EP2010180A4/en not_active Withdrawn
- 2007-04-20 BR BRPI0710559-2A patent/BRPI0710559A2/pt not_active IP Right Cessation
- 2007-04-20 RU RU2008145871/04A patent/RU2008145871A/ru not_active Application Discontinuation
- 2007-04-20 JP JP2009506793A patent/JP2009534420A/ja active Pending
-
2008
- 2008-10-12 IL IL194700A patent/IL194700A0/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JP2009534420A (ja) | 2009-09-24 |
| US8097626B2 (en) | 2012-01-17 |
| IL194700A0 (en) | 2009-08-03 |
| AU2007240364A1 (en) | 2007-11-01 |
| BRPI0710559A2 (pt) | 2011-08-16 |
| EP2010180A4 (en) | 2010-10-13 |
| WO2007124423A2 (en) | 2007-11-01 |
| CN101495113A (zh) | 2009-07-29 |
| US20090298810A1 (en) | 2009-12-03 |
| MX2008013599A (es) | 2008-10-31 |
| WO2007124423A3 (en) | 2009-04-09 |
| CA2650007A1 (en) | 2007-11-01 |
| EP2010180A2 (en) | 2009-01-07 |
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| Date | Code | Title | Description |
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| FA94 | Acknowledgement of application withdrawn (non-payment of fees) |
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